4-(2-Bornyloxy)-2-butyn-1-ol and organoleptic uses thereof

ABSTRACT

Described is the 4-(2-bornyloxy)-2-butyn-1-ol of our invention defined according to the structure:   &lt;IMAGE&gt;   as well as methods for augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles by adding thereto an aroma augmenting or enhancing quantity of the 4-(2-bornyloxy)-2-butyn-1-ol of our invention.

This application is a continuation-in-part of application for U.S.Letters Patent, Ser. No. 574,150 filed on Jan. 26, 1984, now U.S. Pat.No. 4,521,634 which, in turn, is a continuation-in part of applicationfor U.S. Letters Patent, Ser. No. 533,915 filed on Sept. 19, 1983,which, in turn, is a continuation-in-part of application for U.S.Letters Patent, Ser. No. 507,292 filed on Aug. 1, 1983, abandoned.

BACKGROUND OF THE INVENTION

The instant invention provides the 4-(2-bornyloxy)-2-butyn-1-ol of ourinvention defined according to the structure: ##STR2## as well as theuse thereof for augmenting or enhancing the aroma of perfumecompositions, colognes and perfumed articles.

Inexpensive woody, patchouli-like aromas with woody, camphoraceous,patchouli-like and cedar-like topnotes are highly desirable in the artof perfumery. Many of the natural materials which provide suchfragrances and contribute desired nuances to perfumery compositions aswell as perfumed articles including solid or liquid anionic, cationic,nonionic or zwitterionic detergents, perfumed polymers, fabric softenercompositions, fabric softener articles, hair preparations, cosmeticpowders and the like are high in cost, vary in quality from one batch toanother and/or are generally subject to the usual variations of naturalproducts.

Nothing in the prior art suggests the 4-(2-bornyloxy)-2-butyn-1-ol ofour invention or organoleptic uses of same.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is the GLC profile for the crude reaction product of Example Icontaining the compound having the structure: ##STR3## (conditions:SE-30 column programmed at 100°-220° C. at 8° C. per minute).

FIG. 2 is the GLC profile for bulked Fractions 2 and 3 of the firstdistillation of the reaction product of Example I containing thecompound having the structure: ##STR4## (conditions: SE-30 columnprogrammed at 100°-220° C. at 8° C. per minute).

FIG. 3 is the NMR spectrum for Fraction 2 of the second distillation ofthe reaction product of Example I containing the compound having thestructure: ##STR5## (conditions: Field strength: 100 MHz; Solvent:CFCl₃).

THE INVENTION

The present invention provides the 4-(2-bornyloxy)-2-butyn-1-ol havingthe structure: ##STR6##

The present invention also provides a process for preparing the4-(2-bornyloxy)-2-butyn-1-ol by reacting camphene with1,4-dihydroxy-2-butyne in the presence of an appropriate catalyst toform the 4-(2-bornyloxy)-2-butyn-1-ol of our invention in accordancewith the reaction: ##STR7##

Thus, the process of our invention involves the reaction of camphenedefined according to the structure: ##STR8## with 1,4-dihydroxy-2-butynehaving the structure: ##STR9##

The resulting 4-(2-bornyloxy)-2-butyn-1-ol of our invention having thestructure: ##STR10## produced according to the process of our inventionis capable of augmenting or enhancing woody, patchouli-like aromas withwoody, camphoraceous, patchouli-like and cedar-like topnotes of perfumecompositions, colognes and perfumed articles (including soaps, anionic,cationic, nonionic or zwitterionic detergents, fabric softenercompositions, fabric softener articles, optical brightener compositions,perfumed polymers, hair preparations and the like) thus fulfilling aneed in the field of perfumery as well as detergents, colognes, fabricsofteners and cosmetics manufacture.

The reaction of camphene with the 1-4-dihydroxy-2-butyn, to wit:##STR11## takes place in the presence of a catalyst which is a Lewisacid, for example, boron trifloride etherate at temperatures in therange of from about 60° C. up to about 100° C. and at pressures in therange of from about 1 atmosphere up to about 10 atmospheres. Preferably,the reaction takes place at 80° C. at atmospheric pressure and at refluxconditions. The reaction time may vary from about two hours up to abouttwenty hours depending upon the temperature of reaction. Highertemperatures of reaction give rise to lower times of reaction and lowertemperatures of reaction require higher times of reaction but a betteroverall yield. The mole ratio of 1,4-dihydroxy-2-butyn having thestructure: ##STR12## to camphene having the structure: ##STR13## mayvary from about 1:2 up to about 3:1 with a mole ratio of diol:campheneof about 2:1 being preferred. At the end of the reaction, the reactionmass is neutralized and the reaction product defined according to thestructure: ##STR14## is purified for ultimate utility as a perfumant asby means of fractional distillation.

The 4-(2-bornyloxy)-2-butyn-1-ol prepared in accordance with the processof our invention and one or more auxiliary perfume ingredientsincluding, for example, alcohols, other than the4-(2-bornyloxy)-2-butyn-1-ol of our invention, ketones, aldehydes,terpinic hydrocarbons, nitriles, esters, lactones, natural essentialoils and synthetic essential oils may be admixed so that the combinedodors of the individual components produce a pleasant and desiredfragrance, particularly and preferably in woody and patchoulifragrances. Such perfume compositions usually contain (a) the main noteor the "bouquet" or foundation stone of the composition; (b) modifierswhich round off and accompany the main note; (c) fixatives which includeodorous substances which lend a particular note to the perfumethroughout all stages of evaporation and substances which retardevaporation; and (d) topnotes which are usually low boiling, freshsmelling materials.

In perfume compositions, it is the individual components whichcontribute to their particular olfactory characteristics, however, theoverall sensory effect of the perfume composition will be at least thesum total of the effects of each of the ingredients. Thus, the4-(2-bornyloxy)-2-butyn-1-ol of our invention prepared in accordancewith the process of our invention can be used to alter, modify orenhance the aroma characteristics of a perfume composition, for example,by utilizing or moderating the olfactory reaction contributed by anotheringredient in the composition.

The amount of the 4-(2-bornyloxy)-2-butyn-1-ol of our invention preparedin accordance with the process of our invention, which will be effectivein perfume compositions as well as perfumed articles (e.g., anionic,cationic, nonionic or zwitterionic solid or liquid detergents, soaps,fabric softener compositions, drier-added fabric softener articles,optical brightener compositions, perfumed polymers, textile sizingagents and the like) and colognes depends on many factors, including theother ingredients, their amounts and the effects which are desired. Ithas been found that perfume compositions containing as little as 0.01%of the 4-(2-bornyloxy)-2-butyn-1-ol of our invention or even less (e.g.,0.005%) can be used to impart, augment or enhance woody andpatchouli-like aromas with woody, camphoraceous, patchouli-like andcedar-like topnotes in or to soaps, cosmetics, solid or liquid anionic,cationic, nonionic or zwitterionic detergents, fabric softenercompositions, fabric softener articles, optical brightener compositions,textile sizing compositions, perfumed polymers or other products. Theamount employed can range up to 70% of the fragrance components and willdepend on considerations of cost, nature of the end product, the effectdesired on the finished product and the particular fragrance sought.

The 4-(2-bornyloxy)-2-butyn-1-ol of our invention is useful (taken aloneor together with other ingredients in perfume compositions) as (an)olfactory component(s) in detergents and soaps, space odorants anddeodorants, perfumes, colognes, toilet water, bath preparations, such ascreams, deodorants, hand lotions and sun screens; powders, such astalcs, dusting powders, face powders and perfumed polymers and articlesof manufacture produced from said perfumed polymers, e.g., garbage bags,children's toys and the like. When used as an olfactory component inperfumed articles, as little as 0.1% of the 4-(2-bornyloxy)-2-butyn-1-olof our invention prepared in accordance with the process of ourinvention will suffice to impart, augment or enhance woody, andpatchouli-like aromas with woody, camphoraceous, patchouli-like andcedar topnotes. Generally, no more than 6% of the4-(2-bornyloxy)-2-butyn-1-ol of our invention based on the ultimate endproduct is required in the perfumed article. Accordingly, the range of4-(2-bornyloxy)-2-butyn-1-ol in the perfumed article is from about 0.1%by weight of the 4-(2-bornyloxy)-2-butyn-1-ol up to about 6% by weightof the 4-(2-bornyloxy)-2-butyn-1-ol based on the total weight of theperfumed article.

In addition, the perfume composition or fragrance composition of ourinvention can contain a vehicle or carrier for the4-(2-bornyloxy)-2-butyn-1-ol. The vehicle can be a liquid such as anon-toxic alcohol, e.g., ethyl alcohol, a non-toxic glycol, e.g.,propylene glycol or the like. The carrier can also be an absorbentsolid, such as a gum (e.g., gum arabic, guar gum, xanthan gum) orcomponents for encapsulating the composition (such as, for example,gelatin as by coacervation or such as a urea formaldehyde prepolymerwhich on polymerization forms a capsule shell around a liquid perfumecenter).

Our invention also relates to the utilization of controlled releasetechnology for the controlled release of perfumes into gaseousenvironments from polymers such as mixtures of epsilon polycaprolactonepolymers and polyethylene which polyepsilon caprolactone polymers aredefined according to at least one of the structures: ##STR15## wherein"n" is from about 50 up to about 1,200 with the proviso that the average"n" in the system varies from about 150 up to about 700 according to themathematical statement:

    [700≧η≧150]

with the term

    η

being the average number of repeating monomeric units for the epsilonpolycaprolactone polymer. The perfumed material's release rate from suchpolymer mixture is close to "zero order". As a general rule, the releaserate in a polymeric matrix is proportional to t^(-1/2) until about 60%of the functional fluid is released from the polymeric matrix. Therelease rate thereafter is related exponentially to time as a generalrule according to the equation: ##EQU1## wherein k₁ and k₂ areconstants. According to Kydonieus, "Controlled Release Technologies:Methods, Theory, and Applications" (cited, supra) the amount of perfumecomposition released is proportional to time as long as theconcentration of perfume material present, e.g., the4-(2-bornyloxy)-2-butyn-1-ol of our invention is higher than thesolubility of the agent in the matrix. Thus, such dispersed systems aresimilar to the dissolved systems except that instead of a decreasedrelease rate after 60% of the perfume material has been emitted, therelationship holds almost over the complete release curve. Kydonieusfurther states, that if one assumes that the release of functional fluidby diffusion is negligible in monolithic erodible systems, the speed oferosion will control the release rate and release by erosion by asurface-area-dependent phenomenon, the release being constant (zeroorder) as long as the surface area does not change during the erosionprocess. This is the case with the polymers containing the4-(2-bornyloxy)-2-butyn-1-ol of our invention.

The polyepsilon caprolactone polymers useful in practicing our inventionare more specifically described in the brochure of the Union CarbideCorporation, 270 Park Avenue, New York, N.Y. 10017, entitled "NewPolycaprolactone Thermoplastic Polymers PCL-300 and PCL-700". Thesepolyepsilon caprolactone polymers are composed of a repeating sequenceof non-polar methylene groups and relatively polar ester groups. Theaverage number of repeating monomeric units varies between 150 and 700depending on the particular "PCL" number. Thus, regarding PCL-300 theaverage number of repeating monomeric units is 300. Regarding PCL-700,the average number of repeating monomeric units is 700.

The polyepsilon caprolactone homopolymers which are ultimately taken inadmixture with such materials as polyethylene useful in the practice ofour invention may also be stabilized using stabilizers as defined inU.S. Pat. No. 4,360,682 issued on Nov. 23, 1982, the specification forwhich is incorporated herein by reference. The stabilizing materialswhich stabilized the polyepsilon caprolactone useful in conjunction withour invention against discoloration are dihydroxybenzenes suchhydroquinone or compounds having the formula: ##STR16## in which R₁ isalkyl of from 1 to 8 carbon atoms, and R₂ is hydrogen or alkyl of 1 to 8carbon atoms. It is preferable to have such stabilizer in thepolyepsilon caprolactone homopolymer in an amount of from about 100 to500 ppm. Such stabilizers do not interfere with the functional fluidsdissolved and/or absorbed into the polymeric matrix.

The method of incorporating the 4-(2-bornyloxy)-2-butyn-1-ol of ourinvention or perfume compositions containing same into the polymers maybe according to the techniques of U.S. Pat. No. 3,505,432 issued on Apr.7, 1970 (the specification for which is incorporated by referenceherein) or U.S. Pat. No. 4,247,498 issued on Jan. 27, 1981, thedisclosure of which is incorporated by reference herein.

Thus, for example, a first amount of liquid polyethylenepolyepsiloncaprolactone polymer mixture (50:50) is mixed with the4-(2-bornyloxy)-2-butyn-1-ol of our invention. Drops are formed from themixture and the drops are then melted, if desired, with a second amountof unscented low density polyethylene, for example, or polypropylene,for example. Usually, but not necessarily, the second amount of polymeris larger than the first amount. The resulting mixture thus obtained, issolidified subsequent to or prior to ultimate casting into a utilitarianshape.

Thus, in accordance with one aspect of our invention, the imparting ofscent is effected in two stages. In a first stage, a 50:50(weight:weight) polyepsilon caprolactone, e.g., PCL-700: polyethylene inmolten form is admixed with a high percentage of the4-(2-bornyloxy)-2-butyn-1-ol of our invention and the mixture issolidified in the form of pellets or beads. These pellets or beads thuscontain a high percentage of the 4-(2-bornyloxy)-2-butyn-1-ol (e.g., upto 45% by weight of the entire mixture) and may be used as "masterpellets" which thereafter, in a second stage, if desired, may be admixedand liquified with additional polymers such as additional polyethyleneor mixtures of polyethylene and polyepsilon caprolactone in an unscentedstate, or unscented polypropylene. In addition, additional polymers orcopolymers may be used, for example, copolymers specified and describedin United Kingdom Patent Specification No. 1,589,201 published on May 7,1981, the specification for which is incorporated by reference herein.

In accordance with the present invention the4-(2-bornyloxy)-2-butyn-1-ol of our invention is added to the polymer ina large closed container or drum which is maintained under controlledtemperature conditions while the polymer in a melted condition is mixedwith the 4-(2-bornyloxy)-2-butyn-1-ol under agitation.

In order that the perfume be added uniformly to the polymer, thetemperature of the melt is constantly controlled during the process. Thepolymer-perfume mixture is then directed through an elongated conduit orpipe element having a plurality of orifices adjacent to the lower mostportion thereof. The polymer enriched by the4-(2-bornyloxy)-2-butyn-1-ol of our invention is permitted to dripthrough the orifices onto a continuously moving, cooled conveyor uponwhich the polymer containing the 4-(2-bornyloxy)-2-butyn-1-ol of ourinvention solidifies into small size pellets with the perfume imprisonedtherein. The apparatus useful in conjunction with this process,advantageously includes a conveyor of a material which will not adhereto the polymer which contains the 4-(2-bornyloxy)-2-butyn-1-ol of ourinvention.

In order that droplets form into uniform pellets or beads, the conveyoris continuously washed with a liquid, such as water to maintain thesurface relatively cool. The pellets are delivered by the conveyor intoa container and packaged for shipment.

The following Example I illustrates a process for preparing the4-(2-bornyloxy)-2-butyn-1-ol of our invention having the structure:##STR17## Examples II, et seq are illustrative of the organolepticutilities of the 4-(2-bornyloxy)-2-butyn-1-ol of our invention.

All parts and percentages given herein are by weight unless otherwisespecified.

EXAMPLE I Preparation of 4-(2-bornyloxy)-2-butyn-1-ol

Reaction: ##STR18##

Into a 5-liter reaction vessel equipped with stirrer, thermometer,reflux condenser and heating mantle are placed 2510 grams of camphene(14.76 moles) and 1188 grams of 2-butyne-1,4-diol (16.97 moles). Thereaction mass is heated to 56° C. and over a period of 15 minutes, 2 mlof boron trifluoride is added thereto. The reaction mass is then heatedto reflux (135° C.) and refluxed for a period of ten hours. At the endof the ten hour period, an additional 10 ml BF 3 is added and thereaction mass is heated to reflux for an additional three hours. Thereaction mass is then cooled and the crude reaction product is washedwith saturated sodium carbonate solution until neutral. The aqueousphase is separated from the organic phase. The aqueous phase isextracted with toluene and the toluene extracts are added to the organicphase. The resulting organic material is then charged to an evaporatorand the toluene solvent is recovered.

The resulting product is then distilled on a splash column packed withsaddles yielding the following fractions:

    ______________________________________                                                  Vapor        Liquid  Vacuum                                         Fraction  Temp.        Temp.   mm/Hg.                                         No.       (°C.) (°C.)                                                                          Pressure                                       ______________________________________                                        1         25/140       94/164  1.6/1.6                                        2         150          183     9.4                                            3         155          196     1.4                                            4         172          210     1.4                                            ______________________________________                                    

Fractions 2, 3 and 4 are bulked and redistilled on a 12" Goodloe columnyielding the following fractions:

    ______________________________________                                                  Vapor    Liquid     Vacuum Reflux                                   Fraction  Temp.    Temp.      mm/Hg. Ratio                                    No.       (°C.)                                                                           (°C.)                                                                             Pressure                                                                             R/D                                      ______________________________________                                        1          89/133  177/172    1.6    7.3                                      2         139      175        1.5    7.3                                      3         139      179        1.4    7.3                                      4         140      179        1.4    7.3                                      5         140      182        1.4    7.3                                      6         140      180        1.4    7.3                                      7         138/140  187/190    1.6    7.3                                      8         140      175        1.6    7.3                                      9         140      185        1.6    7.3                                      10        140      190        1.6    7.3                                      11        140      190        1.6    7.3                                      12        138      178        1.3    7.3                                      13        138      178        1.3    7.3                                      14        141      190        1.3    7.3                                      15        142      197        1.3    7.3                                      16        147      210        1.3    7.3                                      17        144      216        1.3    7.3                                      ______________________________________                                    

Bulked Fractions 3-16 have an excellent woody and patchouli aroma whichis very long-lasting with excellent woody, camphoraceous, patchouli-likeand cedar nuances.

FIG. 1 is the GLC profile for the crude reaction product prior todistillation (conditions: SE-30 column programmed at 100°-220° C. at 8°C. per minute).

FIG. 2 is the GLC profile for bulked Fractions 2 and 3 of the firstdistillation (conditions: SE-30 column programmed at 100°-220° C. at 8°C. per minute).

FIG. 3 is the NMR spectrum for Fraction 2 of the second distillation(conditions: Field strength: 100 MHz; Solvent: CFCl₃).

EXAMPLE II Perfume Formulation

The following woody cologne, perfume formulation is prepared:

    ______________________________________                                        Ingredients            Parts by Weight                                        ______________________________________                                        Bergamot oil           150                                                    Orange oil             200                                                    Lemon oil              50                                                     Eugenol                10                                                     4-(4-methyl-4-hydroxy amyl)                                                                          40                                                     Δ.sup.3 cyclohexene carboxaldehyde                                      Ylang oil               2                                                     Petitgrain Paraguay    10                                                     Gamma methyl ionone    20                                                     Vetiver Venezuela      18                                                     3α-Methyl-dodecahydro-6,6,9a-                                                                   5                                                     trimethylnaptho-[2,1-b] furan                                                 Product produced by the reaction of                                                                   5                                                     acetic anhydride, polyphosphoric                                              acid and 1,5,9-trimethyl cyclodode-                                           catriene-1,5,9 according to the process                                       of Example I of U.S. Letters Patent                                           3,718,697, the specification for which                                        is incorporated by reference herein                                           Octahydro-9,9-dimethyl-1,6-methano-                                                                  50                                                     naphthalene-1-(2H)ol produced                                                 according to Example III of U.S. Letters                                      Patent 3,996,169, the specification                                           for which is incorporated by reference                                        herein                                                                        The compound having the structure:                                                                   12                                                      ##STR19##                                                                    prepared according to Example I                                               bulked Fractions 3-16                                                         ______________________________________                                    

The compound having the structure: ##STR20## prepared according toExample I imparts an excellent long-lasting woody, patchouli-like aromato this "woody cologne" composition. Accordingly, the composition can bedescribed as "woody cologne" with woody and patchouli-like undertonesand woody, camphoraceous, patchouli-like and cedar topnotes.

EXAMPLE III Preparation of Cosmetic Powder Compositions

Cosmetic powder compositions are prepared by mixing in a ball mill 100grams of talcum powder with 0.25 grams of each of the substances setforth in Table I below. Each of the cosmetic powder compositions has anexcellent aroma as described in Table I below:

                  TABLE I                                                         ______________________________________                                        Substance              Aroma Description                                      ______________________________________                                         ##STR21##             A woody and patch- ouli aroma with woody,                                     camphora- ceous, patchouli-like and cedar                                     topnotes.                                              Perfume composition of Example II.                                                                   A "woody cologne"                                                             with woody and                                                                patchouli-like                                                                undertones and                                                                woody, camphora-                                                              ceous patchouli-like                                                          and cedar topnotes.                                    ______________________________________                                    

EXAMPLE IV Perfumed Liquid Detergent

Concentrated liquid detergents with aromas as set forth in Table I ofExample III (which detergents are prepared from Lysine salt of n-dodecylbenzene sulfonic acid as more specifically described in U.S. LettersPatent, Ser. No. 3,948,818 issued on Apr. 6, 1976, the specification forwhich is incorporated by reference herein) are prepared containing eachof the substances set forth in Table I of Example III, supra. They areprepared by adding and homogeneously mixing the appropriate quantity ofperfumery substance as set forth in Table I of Example III in the liquiddetergent. The detergents all possess aromas as set forth in Table I ofExample III the intensity increasing with greater concentrations ofperfumery substance of Table I of Example III, supra.

EXAMPLE V Preparation of a Cologne and Handkerchief Perfume

The perfume substances of Table I of Example III, supra are incorporatedinto colognes at concentrations of 1.5%, 2.0%, 2.5%, 3.0% and 4.0% in80%, 85%, and 90% aqueous ethanol; and into a handkerchief perfumecomposition at concentrations of 10%, 15%, 20%, 25% and 30% (in 85%, 90%and 95% aqueous ethanol). Distinct and definitive aromas as set forth inTable I of Example III are imparted to the cologne and to thehandkerchief perfume compositions.

EXAMPLE VI Preparation of a Detergent Composition

A total of 100 grams of a detergent powder (a nonionic detergent powdercontaining a proteolytic enzyme prepared according to Example I ofCanadian Letters Patent No. 985,190 issued on Mar. 9, 1976, thedisclosure of which is incorporated by reference herein) is mixed with0.15 grams of each of the substances set forth in Table I of ExampleIII, supra, until substantially homogeneous compositions are obtained.These compositions have excellent aromas as set forth in Table I ofExample III.

EXAMPLE VII Preparation of Soap

Each of the perfumery substances of Table I of Example III areincorporated into soap (LVU-1) at 0.1% by weight of each substance.After two weeks in the oven at 90° F., each of the soaps showed novisual effect from the heat. Each of the soaps manifested an excellentaroma as set forth in Table I of Example III, supra.

EXAMPLE VIII Preparation of Soap Composition

One hundred grams of soap chips (IVORY®, registered trademark of theProcter & Gamble Co. of Cincinnati, Ohio) are mixed individually withone gram each of the perfumery substances of Table I of Example III,supra, until a homogeneous composition is obtained. The homogeneouscomposition is then treated under three atmospheres pressure at 180° C.for a period of three hours and the resulting liquid is placed into asoap mold. The resulting soap cakes, on cooling, manifest excellentaromas as set forth in Table I of Example III, supra.

EXAMPLE IX Preparation of a Solid Detergent Composition

A detergent is prepared from the following ingredients according toExample I of Canadian Letters Patent No. 1,007,948, the specificationfor which is incorporated by reference herein:

    ______________________________________                                        Ingredients        Parts by Weight                                            ______________________________________                                        "Neodol 45-II" (a C.sub.14 -C.sub.15                                                             12                                                         (alcohol ethoxylated with                                                     11 moles of ethylene oxide)                                                   Sodium carbonate   55                                                         Sodium citrate     20                                                         Sodium sulfate, water                                                                            q.s.                                                       brighteners                                                                   ______________________________________                                    

This detergent is a "phosphate-free" detergent. A total of 100 grams ofthis detergent is admixed separately with 0.15 grams of each of theperfume substances of Table I of Example III, supra. The detergentsamples each have excellent aromas as set forth in Table I of ExampleIII, supra.

EXAMPLE X

Utilizing the procedure of Example 1 at column 15 of U.S. Pat. No.3,632,396 (the specification for which is incorporated by referenceherein), a non-woven cloth substrate useful as a dryer-added fabricsoftening article of manufacture is prepared, wherein the substrate, thesubstrate coating and the outer coating and the perfuming material areas follows:

1. a water "dissolvable" paper ("Dissolvo Paper")

2. Adogen 448 (m.p. about 140° F.) as the substrate coating; and

3. an outer coating having the following formulation (m.p. about 150°F.);

57 percent C₂₀₋₂₂ HAPS

22 percent isopropyl alcohol

20 percent antistatic agent

1 percent of one of the perfume substances of Table I of Example III,supra.

A fabric softening composition prepared as set forth above having theabove aroma characteristics as set forth in Table I of Example III,supra, essentially consists of a substrate having a weight of about 3grams per 100 square inches, a substrate coating of about 1.85 grams per100 square inches of substrate and an outer coating of about 1.4 gramsper 100 square inches of substrate, thereby providing a total aromatizedsubstrate and outer coating weight ratio of about 1:1 by weight ofsubstrate. The aroma set forth in Table I of Example III is imparted ina pleasant manner to the headspace in the dryer on operation thereof,using said dryer-added fabric softening non-woven fabric.

What is claimed is:
 1. The 4-(2-bornyloxy)-2-butyn-1-ol having thestructure: ##STR22##
 2. A process for augmenting or enhancing the aromaof a consumable material selected from the group consisting of perfumecompositions, colognes and perfumed articles comprising the step ofintimately admixing with said consumable material an aroma augmenting orenhancing quantity of the 4-(2-bornyloxy)-2-butyn-1-ol defined accordingto claim
 1. 3. The process of claim 2 wherein the consumable material isa perfume composition or cologne.
 4. The process of claim 2 wherein theconsumable material is a perfumed article and the perfumed article is asolid or liquid anionic, cationic, nonionic or zwitterionic detergent.5. The process of claim 2 wherein the consumable material is a perfumedarticle and the perfumed article is a perfumed polymer.
 6. The processof claim 2 wherein the consumable material is a perfumed article and theperfumed article is a fabric softener composition or drier-added fabricsoftener article.
 7. The process of claim 2 wherein the consumablematerial is a perfumed article and the perfumed article is a cosmeticpowder.